Isopropyl iodide

Isopropyl iodide
Skeletal formula of isopropyl iodide
Spacefill model of isopropyl iodide
Names
Preferred IUPAC name
2-Iodopropane[1]
Identifiers
3D model (JSmol)
1098244
ChemSpider
ECHA InfoCard 100.000.782 Edit this at Wikidata
EC Number
  • 200-859-3
MeSH isopropyl+iodide
RTECS number
  • TZ4200000
UNII
UN number 2392
  • InChI=1S/C3H7I/c1-3(2)4/h3H,1-2H3 ☒N
    Key: FMKOJHQHASLBPH-UHFFFAOYSA-N checkY
  • CC(C)I
Properties
C3H7I
Molar mass 169.993 g·mol−1
Appearance Colourless liquid
Density 1.703 g mL−1
Melting point −90.00 °C; −130.00 °F; 183.15 K
Boiling point 88.8 to 89.8 °C; 191.7 to 193.5 °F; 361.9 to 362.9 K
1.4 g L−1 (at 12.5 °C)
Solubility in chloroform Miscible
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
Solubility in benzene Miscible
890 nmol Pa−1 kg−1
1.4997
Viscosity 6.971 mPa (at 20 °C)
Thermochemistry
137.3 J K−1 mol−1
−77.2–−72.6 kJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Warning
H226, H302
Flash point 42 °C (108 °F; 315 K)
Related compounds
Related alkanes
Related compounds
 Diiodohydroxypropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isopropyl iodide is the organoiodine compound with the formula (CH3)2CHI. It is colorless, flammable, and volatile. Organic iodides are light-sensitive and take on a yellow colour upon storage, owing to the formation of iodine.

Preparation

Isopropyl iodide is prepared by iodination of isopropyl alcohol using hydrogen iodide or, equivalently, with a mixture of glycerol, iodine, and phosphorus.[2] An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of sodium iodide (Finkelstein reaction):[3]

(CH3)2CHBr + NaI → (CH3)2CHI + NaBr

References

  1. ^ "isopropyl iodide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 3 March 2012.
  2. ^ Merck Index of Chemicals and Drugs, 9th ed., monograph 5074
  3. ^ Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989
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